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<h1><a href="https://archiveofourown.org/works/22608319">Cassiel Seduces the Guard-Captain</a> by <a class='authorlink' href='https://archiveofourown.org/users/rebirthcorbenik/pseuds/rebirthcorbenik'>rebirthcorbenik</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Dungeons &amp; Dragons (Roleplaying Game)</td></tr>

<tr><td><b>Genre:</b></td><td>Angst, Blow Jobs, Crossdressing, M/M, Oral Sex</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-02-08</td></tr>

<tr><td><b>Updated:</b></td><td>2020-02-08</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-04-28 16:54:59</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,877</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/22608319</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/rebirthcorbenik/pseuds/rebirthcorbenik</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Cassiel pulls a classic DnD move. Seduce someone to get something he wants.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Original D&amp;D Character(s)/Original D&amp;D Character(s)</td></tr>

<tr><td><b>Comments:</b></td><td>1</td></tr>

<tr><td><b>Kudos:</b></td><td>4</td></tr>

</table>

<a name="section0001"><h2>Cassiel Seduces the Guard-Captain</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>We had a fade to black moment in game, and I wanted to expand on it.</p>
    </blockquote></div><div class="userstuff module">
    
    <p>Cassiel was distracted by the slight jingle of coins on his new belt as he and Prudence made their way through the streets of Eden Solum. He wore a black sleeveless dress with a slit up the right leg, a gold sheer top that was affixed to him by a choker, and the jingling belt that held the ensemble together.  He wasn’t used to wearing such decorative clothes, to drawing attention to himself. The clothes themselves had been given to him by Nillen, the proprietor of the Peach Pitt, at Cassiel’s request to be dolled up for the evening. His look was completed with gold bands around his biceps, heavy eye make-up, and luscious red lipstick that Nillen had applied for him.</p>
<p>The small keg of honeyed wine Cassiel was carrying started to become unbearably heavy in his arms. Cassiel and Prudence were off to perhaps gain access to the city’s coveted teleportation circle. Since magic was forbidden within the city without a permit, Cassiel needed to make sure that he and his newly found friends wouldn’t get arrested for using it. </p>
<p>Upon arriving at the Whitestone Congress, Cassiel left Prudence outside as to conduct his business with Guard-Captain Geoffrey Truegust in private. </p>
<p>“Be safe in there,” Prudence called as Cassiel entered the building. </p>
<p>Cassiel gave a wave as he disappeared through the door. He and his friends had talked with Captain Truegust earlier in the day with little luck on securing paperwork for circle access. However, Cassiel made a promise to return later in the evening. Captain Truegust’s secretary, Ms. Tarris, was still at her desk working late into the night as Cassiel approached. </p>
<p>Cassiel gave her a sultry smile, “I told you I’d be back.”</p>
<p>“So you did,” she responded. </p>
<p>“Is Captain Truegust still here?”</p>
<p>“Yes, you can head inside. I put you down for an appointment.”</p>
<p>Cassiel drifted past her desk to the closed, heavy wooden door that stood as a silent guard between the captain and the outside world. Cassiel gathered all of his mental fortitude and quietly opened the door to Truegust’s office. </p>
<p>The guard-captain was a homely man; once delicate half-elven features gave way to years of hard labor under harsh sunlight. He had long, silver-grey hair that was shaved on one side, a square jaw with short stubble, and a long, aquiline nose. He was older and had grown slightly more rotund as the years passed, but the hard muscles and broad shoulders of a foot soldier remained. As the door closed, Captain Truegust looked up from his mountain of paperwork.</p>
<p>“Hello Captain,” began Cassiel. He lifted the little keg of 25 year-old honeyed wine.</p>
<p>Truegust gave Cassiel a questioning look as he polished off the rest of his less than satisfying ale. He placed the tankard on the desk and stood to retrieve a glass for Cassiel. Cassiel tried to make himself look smaller as he was a good six inches taller than the guard-captain. Truegust found a small vase that hadn’t been used in a while and started cleaning it out.</p>
<p>“I assume you’re here to speed up the paperwork for the teleportation circle. I’m quite busy,” Truegust snidely commented as he sank back into his office chair.</p>
<p>“Captain, I only bring you a gift. I heard it was your favorite,” Cassiel said with a wide smile, showing off his sharp canines under plush, blood-colored lips. </p>
<p>Cassiel moved forward opening the tap of the keg to pour Captain Truegust a large helping of the expensive wine. He declined to fill the vase set aside for himself; this was about the captain’s pleasure. Truegust swirled the wine around in his tankard. While he would have preferred a small tasting glass, it was rare to have such a treat. </p>
<p>“This is a good year. I’m surprised you got a hold of it.” There was an unspoken question in the air, lingering on the captain’s mind.</p>
<p>Cassiel seemed to understand where the captain was heading. “Well, I wanted to make a good impression. Hopefully, we can work something out for access to the circle.”</p>
<p>Cassiel’s voice raised to a slightly more feminine timbre as his crimson eyes looked the captain over, finally resting for a few seconds on Truegust’s groin. He let his fingers rest on Geoffrey’s thigh as his eyes fluttered back to the grizzled face. The captain cleared his throat, slightly uncomfortable with such brazen actions. He rose from his desk to cross the room to the large wooden door. Cassiel thought that he had ruined his chances by flirting so openly with a ‘happily’ married man. Silently cursing his forwardness, he waited for Geoffrey to dismiss him from the Congress. However, his ears were greeted with a turn of a lock on the door and a chair being shoved against it for extra security. Captain Truegust turned a deep shade of pink as he walked back and slowly relaxed into his chair. He took a large swig of the honey wine before looking into Cassiel’s eyes with a nod of acceptance. Cassiel noticed that the captain's pupils had enlarged to almost engulf the beautiful blue that rested within. He knelt between the captain’s legs letting his hands rest on the man’s thighs.</p>
<p>“It’s ok. I can be anyone you want me to be,” Cassiel soothed. “You can pretend I’m your lover or your wife.” The words came out of his mouth with years of practice; something he could thank Maescia for. Captain Truegust just nodded, let his eyes close, and his head fall back. </p>
<p>Cassiel started slowly after receiving permission to touch. He reached his slim, dexterous fingers to Geoffrey’s belt, gently tugging it out of place while he started placing kisses along a clothed thigh. The kisses started from the knee and peppered a trail close to the guard’s groin. The captain jerked a bit at the soft touch, but quickly acclimated to the affection. Cassiel quickly released the belt and made his way to the buttons holding the captain within his breeches. He cautiously slipped his hands under Geoffrey’s underclothes to cradle the flaccid dick resting beneath. Cassiel, still pressing kisses to the captain’s legs, withdrew his prize from the confines of the layers of clothes. Truegust sucked air through his teeth when his member was suddenly exposed to the cold air of his office, not expecting to feel himself out in the open so soon. Cassiel stroked Geoffrey’s legs in loving reassurance. </p>
<p>
  <i>This is going to be a bit of a challenge, </i> Cassiel’s thoughts wafted through his brain.
</p>
<p>After a bit of deliberation, he decided to go with a more aggressive approach. Cassiel immediately reached out with his tongue to play with the small bit of foreskin covering the head of Geoffrey’s cock. His tongue reached the crown, swirling around it like it was a treat at a local festival. At the same time, he started stroking the shaft with one hand in time with his licks while the other hand fondled the captain’s balls. Truegust let out a small gasp at the intensity after such a shy start. This only seemed to inspire Cassiel to continue with more fervor. Cassiel sucked the head after a few moments of licking to alternate sensation. He contracted and released the shaft in his hand to further stimulate the captain, adding his overflowing drool to the mix, his messed up lipstick forming a sweet halo around Truegust’s cockhead. Salty pre landed on his lapping tongue, confirming that this was beginning to feel delightful for the good captain. After a few minutes of incessant teasing and the guard-captain falling deeper into delusion, Cassiel felt Geoffrey’s dick fill out. </p>
<p>Cassiel knew the exact moment when Geoffrey started to picture who he wanted between his legs. All of a sudden fingers started wandering through the long strands of Cassiel’s black wig. Rough hands forced his mouth down on to a painfully average six inch erection. Cassiel slightly choked on the sudden intrusion down his throat, but quickly opened his mouth wider to accommodate rougher treatment. Cassiel started to flex his throat muscles around Geoffrey’s cock, taking care to make sure his teeth didn’t scrape it. He had gotten one too many punishments for being careless with them in the past. Cassiel bobbed his head in tune to the hands pulling him back and forth, taking more of the dick each time he went down. He was drooling everywhere and had stopped using his hands on Truegust all together. After a few full thrusts, Geoffrey held the head between his thighs down on his cock. Cassiel took it all with learned grace. He let his tongue hang out, slightly lapping at the base of the captain’s balls while swallowing around the intruding shaft. That seemed to let Truegust know that he could take whatever the man dished out.</p>
<p>Guard-Captain Truegust truly started to thrust into Cassiel’s welcoming mouth as lipstick streaked down his dick and down the sides of the opened mouth between his thighs. His breathing became more labored by the second. Cassiel hummed around the guard’s dick, trying his best not to make any noise to disturb the fantasy permeating the man’s mind. He met Truegust’s hips thrust for thrust, shoving his nose into the messy patch of grey pubes at the base of the guard’s dick. The thrusts came harder and more erratic as the minutes ticked on, and Cassiel’s throat and mouth became more sore the longer they were forcefully opened. Finally, after what seemed like hours of ill-practiced humping, Geoffrey held Cassiel’s head down hard around his dick and shoved his cock as far as it would go down Cassiel’s welcoming mouth. His balls drew up and within a couple of swallows of Cassiel’s velvety throat, the guard-captain came harder than he had in years. Cassiel braced himself against Geoffrey’s thighs as he greedily swallowed all the cum that was pumped down his throat.</p>
<p>“Seven Hells!” </p>
<p>Captain Truegust let his arms fall off of Cassiel’s head to his sides, but Cassiel stayed attached to the cock before him drawing every last bit of spunk into his throat. He only withdrew after the captain’s dick started to soften, a lesson he learned well as a former cockwarmer for some minor noble. Geoffrey raised his right arm to drape over his face in exhaustion or embarrassment; Cassiel couldn’t tell. However, he made no move to speak or look at Cassiel. </p>
<p>
  <i>Ah, one of those types.</i>
</p>
<p>Cassiel finally broke the silence, “Thank you, Captain.” </p>
<p>He stood on shaky knees, wishing there had been some sort of cushion on the floor, and quietly made his way out of the office. He didn’t dare say anything more as he drifted again past Ms. Tarris to the front entrance of the Whitestone Congress. He kept his head down in submission, hoping that no one would question or look at him on the way out. Prudence was right where Cassiel left him thirty minutes prior. He took a minute to compose himself and brush the tears forming in his eyes away. </p>
<p>“Hey, I’m done here. Let’s go talk to the other fucks who need to sign this paperwork,” Cassiel called to Prudence. He only hoped that Prudence couldn’t hear the shaking in his voice.</p>
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